Winter Park Vacation Packages

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Your Winter Park Vacation

When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. Rollins College, Full Sail University and Altamonte Mall are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park vacation plans in motion!

Top Winter Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $736, price is now CA $412 per person
CA $412
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,346 reviews)
Very nice they should have

Reviewed on Aug. 19, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,886, price is now CA $764 per person
CA $764
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,002 reviews)
This was a good time!

Reviewed on Aug. 23, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $853, price is now CA $422 per person
CA $422
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
Will refer to every one

Reviewed on Aug. 24, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,749, price is now CA $1,378 per person
CA $1,378
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $949, price is now CA $534 per person
CA $534
per person
Nov 1 - Nov 8
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on Aug. 24, 2025

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
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Baldwin Park

Baldwin Park might not have many top sights, but Orlando Fashion Square and East Orlando Shopping Center are two attractions nearby that you can check out.

Find hotels in Baldwin Park

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Winter Park Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 10 to Sep 11
CA $128
CA $144 total
Sep 10 - Sep 11
includes taxes & fees
8.2/10 Very Good! (6,555 reviews)
Great place
"This hotel was great. One of the friendliest staff as a whole. Everyone went above and beyond. Clean. Breakfast is overpriced but tasted good."

Reviewed on Aug. 23, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Sep 14 to Sep 15
CA $121
CA $136 total
Sep 14 - Sep 15
includes taxes & fees
8.8/10 Excellent! (2,918 reviews)
"Nice place for a relaxed stay in orlando."

Reviewed on Aug. 23, 2025

Marriott's Grande Vista
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Aug 28 to Aug 29
CA $99
CA $112 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (4,818 reviews)
"Well run, great staff. Very good prices."

Reviewed on Aug. 19, 2025

Rosen Inn at Pointe Orlando
See all 14,607 properties in Winter Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
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Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Winter Park

Aquatica Orlando

Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $105
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $43
per adult
82% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Winter Park

Frequently asked questions

How much does a Winter Park vacation package cost?
You can pick up a vacation package to this destination from CA $412 on Expedia. But how much your vacation to Winter Park costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Winter Park?
January, February and July are great times to look for cheap Winter Park vacation packages. Opting to travel in quieter periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Winter Park?
Allow at least 2 days for your Winter Park vacation if you're hoping to immerse yourself in everything that makes this destination special. Stroll around popular areas, including Northeast Orlando and Ivanhoe Village. Then check out top attractions such as Tinker Field and Dr. Phillips Centre for the Performing Arts. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to go beyond Winter Park? Consider an excursion or two.
Is it worth booking a vacation package to Winter Park?
Winter Park has all the ingredients you need for a fantastic getaway — golfing, shopping and markets are just the start. Whether you want to visit sights like Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, or take the path less travelled, you'll find plenty to experience on your Winter Park vacation.
How to find the best Winter Park package deals?
Bagging a cheap Winter Park package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winter Park package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Winter Park vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Winter Park vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winter Park?
If you're planning a spontaneous Winter Park trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Winter Park?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Winter Park.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Winter Park. Then, select a property that suits your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Winter Park. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Winter Park vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.